Purchase gaskets for your pool skimmer. Many pool supply stores sell the popular gasket sizes for most pool skimmers. You will need two, one for inside the pool wall and one for outside as well.
Lower your water level to several inches below the skimmer. Switch the filter's multi-port valve to the drain setting to drain the pool to the necessary level.
Disassemble the old skimmer. Remove the caulking around the base of the skimmer on the outside of the pool. Remove the skimmer faceplate and set the screws aside. Continue to unscrew the remaining screws from inside the pool that hold the skimmer in place. Unscrew with one hand while holding skimmer. Discard the old gaskets.
Align the rubber gaskets on both sides of the pool wall with the screw holes. Use a small amount of adhesive cement to hold the gaskets in place. Replace the original screws that hold the skimmer in place. Place the screw through the gasket and pool wall. Align the skimmer with the gasket and secure the screw. Repeat with the remaining screws. Do not over-tighten.
Attach the skimmer faceplate and screws over the gasket. Do not over-tighten. Apply silicon caulk around the edges of the skimmer on the outside of the pool only. Refill the pool to the two-thirds point of the skimmer opening's vertical height.